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How To Plan A Weekend Trip, Stress Free

how to plan a weekend tripMaybe you don’t have enough vacation time for a luxurious weeklong getaway. Maybe you’re a caviar girl living on a ramen noodle budget while you save up for bigger and better things. Or maybe mom and dad have kindly agreed to take the kids for the weekend while you sneak away for some much-needed adult time.

Whatever your situation, a weekend getaway is the perfect opportunity to break out of your routine, recharge your batteries and enjoy the inspiration that comes from experiencing a new place. The last thing you want, though, is for it to feel rushed and stressful. With a little planning, you can pull off a weekend trip that feels like an actual vacation and leaves you feeling ready to take on the week ahead.

How To Plan A Weekend Trip, Stress Free

Over the last few years I’ve mastered the 48-hour trip. Between friends getting married, moving to new cities, keeping in touch in with family, and satisfying my wanderlust, there’s been no shortage of reasons to travel. Since I run my own business, though, taking a long vacation requires quite a bit of planning and isn’t always in the budget. Weekend trips are the ideal in-between (plus it’s so much easier to bring pets along, which I love!).

In this post I’ll show you how to plan a weekend trip free of stress and without spending a ton of money.

1. Don’t be afraid to leave the beaten path

When you’re going on a longer trip, there can be pressure to choose the perfect destination. You want somewhere with plenty to do, lots of places to eat, and so on.

The beauty of a weekend getaway is that there’s not that much time, and I look at that as a plus. You can enjoy a quaint one-stoplight town without being there so long you get bored. You can go off the grid and sacrifice cell service for a couple days without losing your mind. It’s also a lot cheaper than visiting a major tourist destination.

Some of my favorite weekend trips have been to small, random towns within a couple hours of where we live, places that I probably never would have visited otherwise.

2. Pick just one thing you really want to do each day

If you’re a planner extraordinaire, I urge you to leave your uber-scheduled ways behind for your weekend trip. If you’re trying to squeeze in a giant itinerary, it’s easy to feel pressured to get it all done and disappointed when you inevitably don’t.

Instead, pick just one thing you really want to do each day and let everything else fall into place around that. For example, plan a morning hike and leave the afternoon free for a leisurely meal and exploring. Or make a reservation for an evening wine tasting and spend the morning waking up slow and taking it easy.

how to plan a weekend getaway

When we visited Tuscaloosa last fall, the Alabama game was the main item on our itinerary

Having just a couple things on your itinerary will help you feel like you made the most of your trip without having to watch the clock. After all, that’s what you’re trying to get away from in the first place.

3. Pack light

Once you take a trip with only a backpack, you’ll never want to go back. Even paring down to a carry-on or weekender bag is freeing.

More stuff = more time spent schlepping = less fun.

I’m working on a post of the perfect packing list for a weekend trip, but in the meantime, build your trip’s wardrobe around these staples, which will cover 99% of events on your itinerary:

  • Black leggings
  • Dark skinny jeans
  • Casual t-shirts
  • One dressy top
  • One versatile jacket
  • One pair versatile shoes (like block heels or cute flats)
  • Sneakers
  • Trip-specific items (swimsuit, ski pants, etc.)
weekend trip packing

My weekend trip go-to’s. The Away Larger Carry On and this Under Armour backpack that I adore

I live with this backpack attached to my back. It goes everywhere with me and holds SO MUCH. Usually I use it to hold my laptop and charger, blowdryer/hair tools, makeup, go-bag (see item #4), hoodie, and any shoes I’m not wearing on my feet to travel.

I also recently took the plunge on the Away Larger Carry-On, and I absolutely love it. It’s more than enough space to pack for a weekend trip and could easily accommodate several days’ more worth of stuff with efficient packing. Use this link to receive $20 off your Away purchase!

4. Have a go-bag

Instead of dragging all your cosmetics out of the shower and medicine cabinet every time you go somewhere, make your packing mindless by putting together a go-bag you only use for traveling. Mine is a very sexy ziploc bag, but there are tons of cute options on Amazon.

packing for a weekend trip

My very enviable go-bag. Yes that’s a thermometer #readyforanything

Keep these items in travel sizes in your go-bag:

  • Deodorant
  • Toothbrush
  • Toothpaste
  • Shampoo
  • Face wash
  • Sunscreen
  • Lotion
  • Razor
  • Advil
  • Q-tips
  • Nail clippers
  • Bobby pins/hair ties

I love that I can just grab this bag and know that all the toiletries I’ll need aside from my makeup are in there and I don’t have to think about it!

5. Focus on experiences

If you’re planning a weekend trip with an eye for affordability, make the most of your budget by focusing on new experiences. You can easily rack up a huge tab having dinner at the best restaurant in town, but even if the food is amazing, it’s something you’ve probably done a million times before.

For the same price, you could experience something totally unique to your destination, like a ghost tour of haunted city buildings or a horseback ride through the forest or taking a class with local artists. These are the kinds of things that take you out of your element and give you a fresh perspective, which really makes a trip memorable.

Plannning a weekend trip

Trying my hand at axe-throwing in the Catskills

6. Set yourself up for when you get back

Do not skip this part! This is an essential step in making your weekend trip stress-free and actually feeling relaxed when you get home.

A couple days before you leave, buy some staples to have on hand when you get back, like a box of pasta and a jar of sauce or a freezer pizza. Make sure you’re stocked up on your Monday morning essentials, like coffee and cereal.

On Friday morning before you leave the house, make your bed and wipe down your bathroom and kitchen counters. If you made a mess while packing, either tidy up or sweep it all into a laundry basket and tuck it out of sight to be dealt with later.

If anxiety is your jam like it is for me, make yourself a to-do list for the following week so you can put all of life’s tasks out of your mind for the weekend and pick up easily where you left off when you get back.

When I don’t take the few extra minutes to do these things, I come home and feel disheveled. They make a world of difference in transitioning easily from Friday afternoon to vacation mode and back to reality Monday morning.

7. Go with the flow

Traffic makes it take forever to get out of town. Flights get delayed and waste half the day. Shit happens. It’s part of life and traveling. The key to a successful weekend trip is to be able to go with the flow and adjust your plans as needed.

Bring a book or have a podcast queued up for unexpected delays. Grab a notebook, a pen and a cup of coffee or a cocktail and journal. Try to be mindful and enjoy the moment (I’m forever working on this one). Like anything in life, taking weekend trips gets easier and more fun the more you do it.

This weekend we’re headed upstate to explore Athens, New York! Where do you want to take your next weekend getaway?

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  • Steph
    April 10, 2019 at 4:18 am

    I wish you could take a weekend getaway here. That said, your packing list nails it. You only need a little to go a long way. My new rule is everything must go with at least 4 other things in my suitcase. Obviously, that’s for longer than a weekend, but the simpler, the better. Miss you!!!!

    • Tami
      April 15, 2019 at 9:53 am

      That is a genius rule! And spoken by the true expert. MISS YOU <3